When I first discovered that some men like to get dressed up as women, my automatic response was “are they just secretly gay?” Now it is clear to me that this reaction was the voice of my prior conditioning speaking. Many of us have been conditioned to believe that men who look like women are gay. In Russia, where I’m from, it’s plain dangerous for a man to dress up as a woman. When I told one of my girlfriends in Russia about the idea of suggesting playful cross-dressing to your man, she responded with “well, that’s a sure way to get punched in the face!”

Through my own experience as a dominatrix, in which I worked intimately with clients who had this proclivity, I very quickly learned that the assumption that a cross-dresser is likely gay is superficial and inaccurate. I have met many crossdressers since my first dungeon days, where there was a dedicated sissy dress-up room. In fact, it should tell you something that this room is a must in every dungeon space. Cross dressing is a popular kink, used for both feminization and humiliation. I got the hang of it quickly and discovered that there’s a whole lot more to the desire to change temporarily into a woman than one might think.

Cross-dressing (and here we refer particularly to men dressing up as women) could hardly have a worse reputation. The idea of a man taking pleasure in putting on a pantyhose often seems laughable, pitiful. We assume a marriage would almost certainly break up the day a wife found her husband in her underwear; and that a manager would lose all authority if his colleagues knew about his enthusiasm for make-up. Within the context of traditional masculinity, ross-dressing seems like an admission of failure. Instead of living up to an ideal of strength, ruggedness and ‘normality’, a man keen to slip on a dress is taken to be a deviant of a particularly alarming sort. Within the shadows of the dungeon, however, men are welcome to explore. Often--and for the same reasons of traditional gender precepts--feminization is used along with other practices as an element of humiliation.

From the start, I found this kink interesting because of its light and playful feel. I still remember my first crossdresser, Scott. He kept in touch with me for a while. He seemed to be always smiling and joyful, charmingly announcing things like “I’m ready to be turned into a sissy!” which would make me laugh. This was where I learned that things that most women really hate, such as slutshaming and gynecological chairs, are actually what is most sought after here. Just like Alice who traveled through the looking-glass, where everything was reversed, including logic, I too was surprised, amused, and intrigued to have found myself in a topsy turvy world of apparently illogical behavior in which the things most women hate are what crossdressed men crave. Humiliation, slutshaming, forced feminization, gynecological exams, catcalling, rape fantasies - here all of a sudden these were desired.

Scott was sweet and kind, he usually showed up with a gift and genuinely enjoyed the idea of being transformed into a girl. Just upon entering the play space, he would really soften up and his eyes would shine with curious expectation, like a child about to receive a treat. I’d quickly find a key to his joy “so, Scotty, how are you going to be sissified today? Into a red mystic woman or into a playful sissy in pink? Or maybe something elegant?” and he would reply “whatever you want, Mistress, I’m yours!” I’d choose an outfit, helping him to put it on on his rather voluptuous body (male “boobs” were an asset when choosing a bra). I’d help him to put on stockings and a garter belt. I’d take time helping him with make-up. While being transformed physically, his emotional personality would also transform. His voice would become different, his gestures and movements would adjust into softer, more fluid ones, his muscles would soften. He’d totally sink into a different persona. We gave her a name - Amanda. Amanda was quite different from Scott. She was a wild woman. He described her as shameless, silly and wild, ready to dance in the rain while joyfully singing refrains such as “Like a virgin, touched for the very first time!”

Scott sought to know what it would feel like to cross his legs in a tight cocktail dress, to walk across a marble floor in a pair of heels, to feel a pink Victoria’s Secret bra strap encasing his back, to put a little silver bracelet around his wrist. On occasion he might extend his play to imagining what it would be like to kiss a man as a woman, to be sexually desired in the way women are. Amanda would sometimes give me an erotic dance performance, spanking herself and seducing me with a lapdance. She’d offer confessions about her slutty fantasies, she “couldn’t wait for a man with a big cock to cum on her face.” She also enjoyed being exposed for erotic humiliation. I’d tie her up to a gynecological exam for a proper inspection, and she’d confess “I feel so ashamed to be exposed like this.” Femininity, vulnerability, and shame - these are powerful subspace triggers. Indeed, I believe the three are so close to one another they are almost inseparable. Once someone is vulnerable, feminine qualities inevitably come into play and, at the same time, shame shows up as this deep, primal wound of “I’m not good enough as I am.” Why then is it so desirable?

I kept observing and analyzing this throughout my career. I remember dressing up another of my submissives, Dennis, in a lingerie dress, placing him in front of the mirror, face to face with himself. Admiring himself in the mirror in a pair of white tights, the cross dresser had an instant erection as he sampled the intense, fascinating feeling of simultaneously being himself and the object of his desire. We both saw it and he grew extremely embarrassed, his breathing and heartbeat skyrocketed. I gave him a warm embrace to comfort him. This embrace would end up being what’s known as a ‘peak moment’ in our session, a moment in which he feels seen, understood and valued at his most vulnerable. Dennis would continue to come see me, always taking a chance at exposing his non-standard appearance, raw emotions, and uncontrollable physical reactions, yet trusting that it’s safe and he won’t be judged. After trust had been established, we’d take this play even further, adding restraints, pain, and humiliation. I’d call him a slut, I’d restrain him in an embarrassing posture with his ass up and spank him.

Later on Dennis and I added ‘shopping humiliation’ to the menu of our adventures. We’d go to a lingerie store and pick out a corset. The salesperson would ask me: “what is your size?” And I’d respond: “me? No, it’s for her,” while pointing at Dennis. He’d get embarrassed. He’d get even more embarrassed when I took him to the dressing room to try it on, and even more so afterwards, when I took him for a show in front of the many women trying on different dresses and lingerie at the store. There he was, hiding his hairy chest under a tight corset which would shape his chest into breasts. We eventually turned it up a few notches by challenging Dennis to flirt with women at a lounge while dressed up as a woman. While all of this was initially terrifying for him, he persisted because he thoroughly enjoyed every bit of these challenges. But why?! Why were vulnerability, femininity, and shame such a commonly sought-after cocktail among my clients? To try and understand this, let’s look at another case in point.

While it was fascinating for me to watch a stern-looking lawyer or wall-street guy transform into a playful girl clad in pink, I became interested in what drove their need. As my practice progressed and my approach to kink grew more refined, I began to implement preliminary consultations as a way of offering a more holistic (and therefore more meaningful) experience. I would familiarize myself with the personality of each client in order to obtain a broader picture of why he is so attracted to exploring this type of kink. During our first consultation, Michael would speak in a very serious, businesslike manner, describing himself as a successful executive and listing all his credentials and achievements to underscore his point. Meeting him, I felt as though I was at a board meeting. He was doing his best to sound just right, yet he was so uptight, his face lifeless. I wanted him to relax a bit and open up, so I tried to smile, joke, and share some of my personal stories. I kept expecting him to match my more casual tone, but he was reluctant. I finally asked him to share his agenda for seeing me and inquired what his fantasy was like. With the same straight face, he said “I’d like to be dressed-up in pink lingerie or a leopard dress, to be called a slut, and to be face slapped.” Still, his face was numb, energetically he remained the same. I inquired directly: “Where is the aliveness in this? Why are you not showing any feeling when we speak? Is there a reason for such mistrust when, after all, you came to see me in order to expose your vulnerable side?” He responded that his father educated him very early in life about how to be successful in business, and had told him the key was never to show your weakness to others, including your feelings and emotions. Things became clearer and I invited him to my space to play.

When we began our actual play, I took my time with a slow relaxation ritual. Tuning my breath into his, feeling him energetically as I held him by the shoulders from behind, while he was naked and kneeling. I used a very sensual bondage tie to make him feel safe and nourished. This allowed his breathing to become deeper and longer, his jaws unclenched and his body grew less tense. A major transformation, however, took place as soon as I changed him into pink lingerie. The change was instant. The serious-businessman mask was gone, his eyes began to shine, I had the impression that a new battery had been placed into him. He now spoke in a very melodic voice, almost songlike. He became animated and moved a lot so I suggested he do some catwalking for me, I was half joking, but he enthusiastically complied. Michael’s alterego, Michaella, was full of erotic energy. She wanted to move her hips a lot, she was constantly playing with her nipples, she wanted to play a seductress and so her catwalk turned into a lapdance. She was swept away by her fiery wave and I was directing it swiftly so as to keep it burning in the right places and ways. The unearthed aliveness had so much explosive power in it, that he seemed just shaken open from inside, like the strong initial rush of an Extasy pill. The energy was enormous. He rejoiced in his expressiveness. We ended up dancing together, at first to some wild beats and eventually ending with more soothing and romantic music. Finally he was exhausted and fell asleep in his savasana.

When he awoke I offered him tea. I could see that he was back to his “normal” persona. He became embarrassed about being dressed up and rushed to the bathroom to change. When he emerged, he had the same straight face he had at the restaurant when we first met. “Wow, I already miss that dancing queen,” I exclaimed and he looked down, irritated, as if I had made a sarcastic remark, and then he quickly switched the subject to a neutral one. His neutral subject of choice was the topic of his expertise, taxes, and before I called for it to stop, he began to educate me on how to do my taxes. Now it was my turn to be irritated, and I gently but firmly ushered him out. I felt a bit sad. All these beautiful revelations, powerful energy, and he is in denial. I’m sure his impulse will call him to crossdress again, but again he’ll treat it like a dream or a trip that has nothing to do with his reality. For me, on the other hand, this journey into his alter ego was a clear calling from his subconscious, which needed acknowledgement, respect and understanding.

Michael’s was a rather uncommon situation - where someone chooses total separation from his own alter ego. Other crossdressers prefer to get close and personal with their second personality. Larry, the man who introduced me to the world of kink in New York City, is an example of someone who has spent a fair amount of time negotiating his boundaries with his other personality, Lora. Larry is an alpha guy, a talented builder, serious motocrosser, and the father of two athletic boys. Lora is an elegant woman, very feminine and submissive, and a total slut. These two characters share the same vehicle, a male body, and each wanted total ownership of it. Lora craved a sex-change so that she can be expressed shamelessly full-time. Larry wanted to remain a motocrosser and avoid serious medical procedures. The journey of trying to understand his own gender identity took him to Peru where he hiked the Andes exploring ancient medicine in search of an answer. Finally, Lora and Larry were able to speak and find their resolution. Larry kept his male body intact while Lora needed to be, and would be, played out from time to time.

I had many different encounters with Lora. She was very playful with diverse interests. She enjoyed exploring pain, bondage, humiliation. She enjoyed sensual tease as well as harsh treatments, she could take electric torture as well as tickle abuse. She basically enjoyed passively receiving any kind of attention, she desired to be desired in all kinds of different ways. When Larry would return, Lora wouldn’t just disappear. She would appear in a more subtle form whenever we had a feminie chat about beauty and guys for example. While more rugged alpha men were usually dismissive or annoyed by this kind of talk, Larry would embrace it with understanding. Feminine qualities such as gentleness with children, fluidity in conversations, sensitivity to feelings, a subtle esthetic understanding of beauty, the ability to expose his own or empathise with others’ vulnerabilities - these were the benefits of having Lora side by side with Larry. Larry would emerge full-power during intellectual debates when mental sharpness was required, and during motorcrossing gigs when courage and determination were necessary qualities. Overall, I found him to be a harmonious example of integrated inner characters. As I went deeper, however, toward the end of my career, aided by all kinds of studies and inner explorations, I began to see various limitations to Larry’s kind of balance. Sure, this level of integration was enough to keep one functioning but how about evolving? Besides, as is commonly the case for crossdressers, there is an addictive tendency to demand ever more exciting adventures. Lora demanded more. She wanted new partners, more pain, more humiliation, more risk. Larry wasn’t at ease with her, and he wasn't fully content without a good dose of “high” for Lora. Something felt trapped there, and although he did a good job managing it well, he wasn’t free.

What was this feminine side really all about? Was it actually an inner woman? Why did they go to such dramatic lengths for her to be seen? Does it mean that to be a well-balanced individual, one has to go to such erotic-exhibitionist extremes in order to claim that balance? Does it mean that the ideal wife would need to walk her man on a leash in fishnet stockings in order for him to embrace his feminine and let go and surrender? Something felt unresolved and I couldn't find any clarification in femdom literature or psychology. I came to notice eventually that this type of crossdresser expressiveness can certainly be beneficial when it’s not the end result, but rather a milestone on the path. Life is not something that ever becomes resolved, figured out, and stable (only death is all that). Life is inherently ever deepening.

When I finally grew bored and exhausted from entertaining my crossdressers in all manner of wildly creative ways, I began to ask - now what? Is this it, is the puzzle solved? It didn’t feel solved, neither for me nor for my crossdressers, but we just didn’t know any better. This precipitated my concluding crisis with Domme work, when I finally exhausted myself and couldn't find the enthusiasm to keep playing. Many of my cross dressers, however, weren’t ready to let me go and asked to just spend some time together to smooth out our separation. When I started seeing them in casual settings, for talk instead of play, the flow took us toward more mindful analysis, either in conversation or during a spontaneous guided imagery self-exploration. To our surprise, these unplanned inner journeys proved revelatory. I was able to see that the constant playing-out of an alter ego would become a distraction from or postponement of the recognition of the real calling underneath it. The alterego’s play is usually so bright, dramatic, ecstatic, and therefore addictive, that one has to really get burned out in order to move beyond it. If this finally happens, however, you get the opportunity to glean something more subtle and profound.

I was having a consultation over tea with Steve who was sharing that his naughty female side wanted a lot of his attention, was so selfish in her need to submit that it prevented him from having an intimate relationship. As he spoke and I actively listened, a cat approached me and said “mieow.” Steve said it was his cat, that this cat found him, that the mom left it as a baby by his door and he had no choice but to adopt it. Now he loves it dearly as one would a closest family member. As he spoke, his eyes welled up and a distinct energy flowed between and through us just at that moment. I repeated the keywords that triggered it: mom abandoned this little kitten… and you took care of it…. As I spoke, he softened up a bit more and froze. I asked - do you see where this is pointing? What does this concept of an “abandoned little kitten” mean to you? Where is this one inside of you? Would you adopt this one? We both felt like we touched upon something vulnerable, some territory where he wasn’t yet so comfortable with. It was noticeable that Steve was both enthusiastic and also clearly in unfamiliar territory.

Over the past few years Steve’s crossdresser alter ego had become his comfort zone, whereas this felt deep, new and scary. In order for this side of him to reveal itself further, he needed the courage to be thrown into the unknown. To open up this deeply encapsulated wound which has a story to tell. The story is so raw and primal, that the exposed identity of a cross dresser becomes a temporary cover up, a substitute revelation. If Bills risks diving even further into the dark mystery of this primal wound, he’d see a fragile part of himself that is in acute terror of separation, yet seeking to be seen, to be recognized, to be valued.

Playing out a crossdresser is a dramatic protest against being imaginatively bound by the particular gender-province we happen to have been born into. The feminized alter egos all have individual stories to share, yet they are very similar in their need to be exuberant, wild, accepted and desired. This is just a mask for their opposite - a frightened little entity that desperately wants to be claimed, like an abandoned newborn. This is the origin of our humanness. This is the connection between eternity and our temporary world of mortals. This is the root of our human nature, which we all share. This is the level on which we all crave connection to one another. Our distorted human conditioning makes us search for this connection in so many shapes and forms - cross dressing is just one of a million ways for our subconscious to demand complete unmasking. The message behind this desire is nothing but a call to return to innocence. To simplicity. To deep rest and to ancient unity. It is the meeting of an immortal ascent, an infinite void with a simple, flawed, mortal humanness. In this meeting, they melt into one and the struggle is over, and there is deep relief. The ultimate satisfaction.

The end result sounds magnificent and is indeed, but the path to it is through all the barriers that separate us from is. Through fears and confusion and shame. Shame in particular is where our cover-up begins, so this gate must be traversed. But practically speaking, what happens if a crossdresser finds the root of his longing? Does the game end there? Does this mask just disappear, along with the need to play out this exciting adventure? Actually, it all becomes refined. The adventure of being human and the strive for the balance of masculine and feminine continues, but the means become more subtle, less explosive. Like orchestral music after a crescendo, when all the instruments join in, finally subsides and only the most sublime sound of a world class violinist remains, and nothing else is needed, only this one precious sound is enough. Similarly, after the wild games are over, one can finally recognize that there is no need to go to such extremes just to be able to play out one’s feminine side. The feminine side is in every subtle detail - in the way one starts a day, or smiles at a stranger, or sips the wine. It’s in every breath, so subtle and yet so inseparable.